Editor’s note: This story first appeared in Bicycle Times Issue #11, published in June 2011. Words by Enrico Caracciolo. Images Courtesy of Cuboimages & TCS.

This is one race that really lives up to its name: The Heroic.

It involves dust, mud and hard work, but there’s more to it than that—there is also a lot of fun and enthusiasm among the participants in this, the most beautiful of cycling tours. Even when they are wearing woolen jerseys, riding heavy steel bikes and carrying spare inner tubes in their shoulder bags, there is still the pecorino cheese and fine wine. And all on the loveliest roads in Tuscany.

This has become a major cult event, which brightens the landscape around Siena even more, as if such a thing was possible. Devised and promoted by the Chianti Cycling Park Association, L’Eroica—the “heroic”—is a contest where final placing counts for little or nothing compared to taking part. In this race, cycling makes a leap back into the past, when it was synonymous with a spirit of adventure. It recalls the pioneers of a sport that once captivated the whole of Italy, such as Gino Bartali and Fausto Coppi (two great Italian cyclists from the late 1940s and early 1950s). Their ideals live on in the weekend of sport, culture, costumes and bicycles from the golden age of cycling.

L’Eroica takes place mostly on dirt roads, on four courses with distances varying from 38 to 200 km, which both depart from and finish in Gaiole in the Chianti region. These dirt roads are the main protagonists in the event, and provide a landscape where the traditional ways still linger. The course is demanding and the participants must be able to suffer and sweat without letting their smiles droop, as they take satisfaction from having spent a day of pure cycling.

The race is a reconstruction of the past, with antique bicycles and cyclists dressed in period costumes, in keeping with the spirit of the occasion. The backup teams for the “heroes” also follow in a convoy of vintage cars and motorcycles. On the day of the contest, sport itself becomes an expression of humanity. L’Eroica coincides with the traditional ritual of the grape harvest. The tour is accompanied by a series of side events, including an exhibition of bicycles that are more than a century old, a display of old books and photographic exhibits on the subject of heroic cycling. Together they transform the main square in Gaiole into a popular gathering place.

The start happens in the “French way”—that is to say, in small groups, and before the sun is fully up. Men and bicycles test one another on the roads, reminding us of an altogether more innocent age when human values were more important, and there was less consumerism and no headlong rush towards modernization and progress. The participants stick to the finer details of this period reconstruction, so that rather than swallow maltodextrin and other energy supplements, they drink wine and eat bread with cold meats and pecorino cheese, and they climb back into the saddle still chewing. Some more organized riders keep chunks of polenta in their pockets, wrapped in pieces of newspaper for snacking along the way.

Notable among the participants is the presence of a few genuine characters from the past, including the great Luciano Berruti from Savona, an authentic cyclist and a collector of veteran bikes. Along with Ermes Leonardi, Medardo Fioresi, Cerica Mark and Idrio Bui (once a teammate of Fausto Coppi), they could never be mistaken for anything other than “heroes.”

For the past three years, the ride has settled on a permanent route through the Terre di Siena, now marked with signposts for cyclists who want to test themselves over 200 kilometers. It passes through Chianti, the Crete Senesi and Val d’Orcia, and completes a journey that encapsulates the artistic essence of the legendary Tuscan landscape. Everything seems to be in harmony on these roads that link undiscovered villages and vineyards, forests and olive groves and ancient town squares and pastures.

We are not talking about flat terrain, but something to inspire slow travel and that allows you to drink in the verdant forests of the Val di Merse. Murlo and its traces of Etruscan civilization are another important sight along the way.

Having crossed the Ombrone and the railway tracks of the Treno Natura line at La Befa, in the “Far West” of the Terra di Siena, you reach the Castiglion del Bosco dirt road. This leads up to the spectacular heights of Montalcino, in the neighborhood of the Lume Spento Pass, which the poet Alfonso Gatto once described as “the windowsill of the apocalypse.”

Between the noble vineyards of the Brunello, you descend gently to the point where the Val d’Orcia meets the Val d’Asso. Near Torrenieri you leave the asphalt and travel down the Via Cosona, one of the most beautiful dirt roads in Tuscany, passing a parade of wide-open spaces before your arrival in the small village of Lucignano d’Asso. You then return to the bottom of the Val d’Asso and make a stop in Saint Giovanni d’Asso, the native land of the truffle—the “white gold” of the Crete.

After another 10 legendary kilometers on the dirt road from Pieve a Salti, you reach Buonconvento, where you cross the Cassia. After a short stretch following the remaining traces of the ancient Roman route of Via Francigena, one returns to the magic of the Crete, along two dirt roads that will linger in the memory and should not be missed from the plans of any traveler who wants to taste the essence of the Sienese landscape: the Montacuto road and the extraordinary Monte Sante Marie road. Between these two short but challenging dirt lanes is a brief return to everyday life in the village of Asciano, an ideal resting place.

Once at Castelnuovo Berardenga, you return to the Chianti. Wheat, mills and flour give way again to vineyards, wine cellars and wine. The final part of the Eroica passes between churches and farms along the Vagliagli road. From Radda you reappear in the gorgeous Chiantigiano countryside and pedal towards Vertine, the last “stone jewel” before you dismount back in the main square in Gaiole, at the end of your heroic ride.

To ride in or watch L’Eroica is a unique occasion in Italy and is a proper “real life” experience, which revives an ancient and long-disappeared spirit, and serves to highlight the aggravation so often found in modern sport. Born almost as a joke, and following a bet between a few friends who were passionate about cycling, it has become a grand celebration of traditional culture, history and sport.

L’Eroica Facts

Anyone wanting to join in or simply to assist with the next edition of L’Eroica can get information by contacting the Siena tourist office (above), or the local volunteer office in Gaiole (+39 577 749 411). The event is organized by the Chianti Cycling Park Association in collaboration with the UISP Cycling League in Siena.

Assistance doesn’t stretch beyond the marking of the route, therefore absolute respect for the rules of the road is required.

The three rest stops are strictly “in period,” so only provide bread, cold meats, figs, grapes, water and wine.

Terre Di Siena By Bicycle

The Eroica route follows several dirt roads. If you don’t want to use these or don’t have the specialist skills needed to ride safely over such terrain, there are alternatives available. Ask the Siena tourist office for its free cycling guide, which contains descriptions of 21 cycle routes in different parts of the province, designed for various categories of cyclist: families, serious cycle tourists, and amateurs.